Fumaric Acid → (S)-2-(1-hydroxybut-2-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazine fumarate

HRID 2363684Notes

Reaction equation

HRID 2363684 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:17][CH:16]=2)[N:10]2[N:27]=[CH:28][C:29]([CH:30]([CH3:32])[CH3:31])=[C:9]2[N:8]=1)[CH2:4][CH3:5].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37]>CCO.CCOCC>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[OH:1][CH2:2][C@@H:3]([NH:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:19][CH:20]=2)[N:10]2[N:27]=[CH:28][C:29]([CH:30]([CH3:31])[CH3:32])=[C:9]2[N:8]=1)[CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 46910590(S)-2-(1-hydroxybut-2-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazine

Product 1

HCID 46910591(S)-2-(1-hydroxybut-2-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazine fumarate

Reagents, catalysts & solvents 1

HCID 21585056Diethyl ether ethanolSolvent

Procedure

The product 4 is treated with fumaric acid in an EtOH/Et2O solution. The fumaric acid salt 5 crystallizes from the reaction medium. Mp=175-177° C. 1H NMR (300 MHz, DMSO-d6): δ 13.12 (bs, 2H, OH), 8.71 (bs, 1H, NH), 8.64 (d, 1H, J=4.1 Hz, Harom), 8.03 (d, 2H, J=8.3 Hz, Harom), 7.92 (d, 1H, J=8.0 Hz, Harom), 7.86 (t, 1H, J=8.0 Hz, Harom) 7.70 (s, 1H, Harom), 7.48 (d, 2H, J=8.3 Hz, Harom), 7.35-7.31 (m, 1H, Harom), 6.62 (s, 2H, ═CH), 6.51 (bs, 1H, NH), 4.67 (bs, 2H, CH2), 4.51 (bs, 1H, OH), 3.82 (bs, 1H, CH), 3.45-3.32 (m, 2H, CH2), 2.90 (hept, 1H, J=6.8 Hz, CH), 1.65-1.35 (m, 2H, CH2), 1.23 (d, 6H, J=6.8 Hz, 2 CH3), 0.84 (t, 3H, J=7.4 Hz, CH3).

Workup

  1. customThe fumaric acid salt 5 crystallizes from the reaction medium

Sources & evidence

ORD record
ord-c3408da0fe50418f837d58f0f7b231cf
Source dataset
uspto-grants-2014_04
Patent number
US08691982B2

Reaction notes

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